CA2612596C - Processus d'hydroformylation - Google Patents
Processus d'hydroformylation Download PDFInfo
- Publication number
- CA2612596C CA2612596C CA2612596A CA2612596A CA2612596C CA 2612596 C CA2612596 C CA 2612596C CA 2612596 A CA2612596 A CA 2612596A CA 2612596 A CA2612596 A CA 2612596A CA 2612596 C CA2612596 C CA 2612596C
- Authority
- CA
- Canada
- Prior art keywords
- temperature
- reaction zone
- carbon
- olefinic
- hydroformylation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 97
- 238000007037 hydroformylation reaction Methods 0.000 title claims abstract description 73
- 238000006243 chemical reaction Methods 0.000 claims abstract description 191
- 239000003054 catalyst Substances 0.000 claims abstract description 72
- 150000001875 compounds Chemical class 0.000 claims abstract description 65
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 42
- 239000000203 mixture Substances 0.000 claims abstract description 33
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 25
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 24
- 150000001868 cobalt Chemical class 0.000 claims abstract description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- 229910017052 cobalt Inorganic materials 0.000 claims description 50
- 239000010941 cobalt Substances 0.000 claims description 50
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 50
- 239000003446 ligand Substances 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 229910052698 phosphorus Inorganic materials 0.000 claims description 11
- 125000004437 phosphorous atom Chemical group 0.000 claims description 9
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 6
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 description 30
- 239000000047 product Substances 0.000 description 29
- 150000001336 alkenes Chemical class 0.000 description 25
- -1 aromatic radicals Chemical class 0.000 description 21
- 150000001299 aldehydes Chemical class 0.000 description 17
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000006227 byproduct Substances 0.000 description 11
- 150000001721 carbon Chemical group 0.000 description 10
- 239000012188 paraffin wax Substances 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 9
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000001923 cyclic compounds Chemical class 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- BCAUVGPOEXLTJD-UHFFFAOYSA-N (2-cyclohexyl-4,6-dinitrophenyl) acetate Chemical compound C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C(OC(=O)C)=C1C1CCCCC1 BCAUVGPOEXLTJD-UHFFFAOYSA-N 0.000 description 1
- AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-N 0.000 description 1
- MMEDJBFVJUFIDD-UHFFFAOYSA-N 2-[2-(carboxymethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1CC(O)=O MMEDJBFVJUFIDD-UHFFFAOYSA-N 0.000 description 1
- KBHRXCWOPXOJIP-UHFFFAOYSA-N 9-phenyl-9-phosphabicyclo[3.3.1]nonane Chemical compound C1CCC2CCCC1P2C1=CC=CC=C1 KBHRXCWOPXOJIP-UHFFFAOYSA-N 0.000 description 1
- HXWCOMBZFBADSS-UHFFFAOYSA-N 9-phenyl-9-phosphabicyclo[4.2.1]nonane Chemical compound C1CC2CCCCC1P2C1=CC=CC=C1 HXWCOMBZFBADSS-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 229910052774 Proactinium Inorganic materials 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001334 alicyclic compounds Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
- VELDYOPRLMJFIK-UHFFFAOYSA-N cyclopentanecarbaldehyde Chemical compound O=CC1CCCC1 VELDYOPRLMJFIK-UHFFFAOYSA-N 0.000 description 1
- ISQVBYGGNVVVHB-UHFFFAOYSA-N cyclopentylmethanol Chemical compound OCC1CCCC1 ISQVBYGGNVVVHB-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- MQIKJSYMMJWAMP-UHFFFAOYSA-N dicobalt octacarbonyl Chemical group [Co+2].[Co+2].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] MQIKJSYMMJWAMP-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- IRUCBBFNLDIMIK-UHFFFAOYSA-N oct-4-ene Chemical compound CCCC=CCCC IRUCBBFNLDIMIK-UHFFFAOYSA-N 0.000 description 1
- 125000005474 octanoate group Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229930015698 phenylpropene Natural products 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000011555 saturated liquid Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000000526 short-path distillation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000013517 stratification Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxo-reaction combined with reduction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Manufacturing Of Magnetic Record Carriers (AREA)
- Paints Or Removers (AREA)
- Magnetic Record Carriers (AREA)
- Catalysts (AREA)
Abstract
La présente invention concerne un processus d'hydroformylation qui consiste à faire réagir une composition comprenant un composé possédant au moins une liaison carbone-carbone oléfinique avec hydrogène et monoxyde de carbone en présence d'un catalyseur d'hydroformylation au cobalt modifié organophosphine, ce processus d'hydroformylation étant effectué dans au moins deux zones de réaction, ces deux zones de réaction comprenant une zone de réaction préalable et une zone de réaction postérieure, la température de la zone de réaction postérieure étant d'au moins 2 °C supérieure à la température régnant dans la zone de réaction préalable et, la température de la zone de réaction postérieure étant comprise entre 140 °C et 120 °C, la température de la zone de réaction préalable étant au moins de 230 °C.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05254142 | 2005-06-30 | ||
| EP05254142.2 | 2005-06-30 | ||
| PCT/EP2006/063719 WO2007003589A1 (fr) | 2005-06-30 | 2006-06-30 | Processus d'hydroformylation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2612596A1 CA2612596A1 (fr) | 2007-01-11 |
| CA2612596C true CA2612596C (fr) | 2013-11-26 |
Family
ID=37103131
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2612596A Expired - Fee Related CA2612596C (fr) | 2005-06-30 | 2006-06-30 | Processus d'hydroformylation |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7329783B2 (fr) |
| EP (1) | EP1899290B1 (fr) |
| JP (1) | JP5070208B2 (fr) |
| CN (1) | CN101228106B (fr) |
| AT (1) | ATE495142T1 (fr) |
| CA (1) | CA2612596C (fr) |
| DE (1) | DE602006019592D1 (fr) |
| WO (1) | WO2007003589A1 (fr) |
| ZA (1) | ZA200711026B (fr) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101589012B (zh) * | 2006-12-21 | 2012-08-22 | 国际壳牌研究有限公司 | 加氢甲酰化方法 |
| JP5465662B2 (ja) * | 2007-05-23 | 2014-04-09 | シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー | ヒドロホルミル化プロセス |
| US8017810B2 (en) | 2007-05-23 | 2011-09-13 | Shell Oil Company | Hydroformulation process |
| US7767862B2 (en) | 2008-08-11 | 2010-08-03 | Shell Oil Company | Ligand, catalyst and process for hydroformylation |
| WO2010079018A1 (fr) * | 2009-01-08 | 2010-07-15 | Exxonmobil Chemical Patents Inc. | Améliorations apportées à des alcools ou se rapportant à ceux-ci |
| WO2012072594A1 (fr) | 2010-11-30 | 2012-06-07 | Shell Internationale Research Maatschappij B.V. | Ligand, catalyseur et procédé d'hydroformylation |
| MX2013007488A (es) | 2010-12-29 | 2013-08-15 | Shell Int Research | Metodo y composicion para recuperacion mejorada de hidrocarburos de una formacion que contiene petroleo crudo. |
| WO2013181083A1 (fr) | 2012-05-29 | 2013-12-05 | Shell Oil Company | Composition détergente pour le linge et son procédé de fabrication |
| KR20160041959A (ko) | 2013-08-08 | 2016-04-18 | 바스프 에스이 | 고압 올레핀 히드로포르밀화 반응기에서 코발트 침착물을 제거하는 방법 |
| WO2015094781A1 (fr) | 2013-12-19 | 2015-06-25 | Dow Technology Investments Llc | Procédé d'hydroformylation |
| KR102310130B1 (ko) * | 2014-09-01 | 2021-10-08 | 삼성전자주식회사 | 착용 가능한 전자 장치 |
| CN110981692A (zh) * | 2019-12-25 | 2020-04-10 | 中国科学院兰州化学物理研究所 | 一种联产异壬醇和碳八烷烃的方法及系统 |
| CN115701418B (zh) * | 2021-08-02 | 2024-05-17 | 中国石油化工股份有限公司 | 醛醇组合物及其制备方法、一种连续制备醛、醇的方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3369050A (en) | 1961-10-06 | 1968-02-13 | Shell Oil Co | Separation, recovery and recycle of the catalyst complex in the oxo process |
| US3420898A (en) | 1965-03-29 | 1969-01-07 | Shell Oil Co | Single stage hydroformylation of olefins to alcohols |
| US3501515A (en) | 1965-03-29 | 1970-03-17 | Shell Oil Co | Bicyclic heterocyclic tertiary phosphine-cobalt-carbonyl complexes |
| US3448157A (en) | 1965-09-27 | 1969-06-03 | Shell Oil Co | Hydroformylation of olefins |
| US3448158A (en) | 1966-01-28 | 1969-06-03 | Shell Oil Co | Hydroformylation of olefins |
| US3904547A (en) * | 1973-06-06 | 1975-09-09 | Gen Electric | Process for recycling a cobalt hydroformylation catalyst |
| US5112519A (en) | 1989-06-05 | 1992-05-12 | Mobil Oil Corporation | Process for production of biodegradable surfactants and compositions thereof |
| US5744649A (en) * | 1995-12-06 | 1998-04-28 | Union Carbide Chemicals & Plastics Technology Corporation | Hydroformylation processes |
| DE19617257A1 (de) * | 1996-04-30 | 1997-11-06 | Hoechst Ag | Verfahren zur Hydroformylierung olefinisch ungesättigter Verbindungen |
| US6482990B1 (en) | 1999-09-06 | 2002-11-19 | Taisho Pharmaceutical Co., Ltd. | Prostaglandin E analogues |
| DE10034360A1 (de) | 2000-07-14 | 2002-01-24 | Oxeno Olefinchemie Gmbh | Mehrstufiges Verfahren zur Herstellung von Oxo-Aldehyden und/oder Alkoholen |
| ATE401292T1 (de) | 2003-10-21 | 2008-08-15 | Basf Se | Verfahren zur kontinuierlichen herstellung von aldehyden |
| DE10357718A1 (de) | 2003-12-09 | 2005-07-21 | Basf Ag | Verfahren zur Herstellung von Tricyclodecandialdehyd |
-
2006
- 2006-06-28 US US11/427,247 patent/US7329783B2/en active Active
- 2006-06-30 JP JP2008518856A patent/JP5070208B2/ja not_active Expired - Fee Related
- 2006-06-30 WO PCT/EP2006/063719 patent/WO2007003589A1/fr not_active Ceased
- 2006-06-30 DE DE602006019592T patent/DE602006019592D1/de active Active
- 2006-06-30 CN CN2006800268536A patent/CN101228106B/zh not_active Expired - Fee Related
- 2006-06-30 AT AT06777527T patent/ATE495142T1/de not_active IP Right Cessation
- 2006-06-30 EP EP06777527A patent/EP1899290B1/fr not_active Revoked
- 2006-06-30 CA CA2612596A patent/CA2612596C/fr not_active Expired - Fee Related
-
2007
- 2007-12-19 ZA ZA200711026A patent/ZA200711026B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20070015942A1 (en) | 2007-01-18 |
| CA2612596A1 (fr) | 2007-01-11 |
| CN101228106B (zh) | 2011-09-14 |
| US7329783B2 (en) | 2008-02-12 |
| ATE495142T1 (de) | 2011-01-15 |
| JP2008544971A (ja) | 2008-12-11 |
| EP1899290A1 (fr) | 2008-03-19 |
| CN101228106A (zh) | 2008-07-23 |
| DE602006019592D1 (en) | 2011-02-24 |
| WO2007003589A1 (fr) | 2007-01-11 |
| ZA200711026B (en) | 2008-11-26 |
| JP5070208B2 (ja) | 2012-11-07 |
| EP1899290B1 (fr) | 2011-01-12 |
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| US6777579B2 (en) | Hydroformylation process | |
| GB2451325A (en) | Hydroformylation process | |
| WO2008074826A1 (fr) | Procédé d'hydroformylation | |
| WO2004056732A1 (fr) | Procede d’hydroformylation en presence d’un additif contenant du soufre | |
| KR20230115501A (ko) | 알코올의 제조방법 |
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